Oxidative
isocyanide-based multicomponent reactions (oxidative IMCRs) are very
useful tools for the rapid construction of molecular diversity starting
from readily available and stable substrates. Despite all their benefits,
such multicomponent reactions are underdeveloped and strictly limited
to 3-component processes. Indeed, in the presence of several reaction
partners, the oxidation event needs to be rigorously chemoselective,
which becomes incredibly more intricate as the number of reactive
components increases. Nonetheless, we could overcome this significant
pitfall and reach the first oxidative Ugi-type 4-IMCR by capitalizing
on a very mild and green TEMPO-catalyzed electro-oxidation process.
Employing alcohols as aldehyde surrogates and in the notable absence
of any supporting electrolyte, this transformation proved to be extremely
chemoselective in the presence of an amine and was compatible with
a wide range of alcohols, amines, isocyanides, and carboxylic acids.
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